KR20000075961A - Fungicidal compositions based on metalyxyl - Google Patents
Fungicidal compositions based on metalyxyl Download PDFInfo
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- KR20000075961A KR20000075961A KR1019997008046A KR19997008046A KR20000075961A KR 20000075961 A KR20000075961 A KR 20000075961A KR 1019997008046 A KR1019997008046 A KR 1019997008046A KR 19997008046 A KR19997008046 A KR 19997008046A KR 20000075961 A KR20000075961 A KR 20000075961A
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- metallaxyl
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- 239000000203 mixture Substances 0.000 title claims abstract description 40
- 230000000855 fungicidal effect Effects 0.000 title claims abstract description 8
- QNBTYORWCCMPQP-JXAWBTAJSA-N (Z)-dimethomorph Chemical compound C1=C(OC)C(OC)=CC=C1C(\C=1C=CC(Cl)=CC=1)=C/C(=O)N1CCOCC1 QNBTYORWCCMPQP-JXAWBTAJSA-N 0.000 claims abstract description 14
- 239000005761 Dimethomorph Substances 0.000 claims abstract description 10
- PCCSBWNGDMYFCW-UHFFFAOYSA-N 5-methyl-5-(4-phenoxyphenyl)-3-(phenylamino)-1,3-oxazolidine-2,4-dione Chemical compound O=C1C(C)(C=2C=CC(OC=3C=CC=CC=3)=CC=2)OC(=O)N1NC1=CC=CC=C1 PCCSBWNGDMYFCW-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 9
- 239000000417 fungicide Substances 0.000 claims description 8
- 230000009545 invasion Effects 0.000 claims description 5
- 241000233866 Fungi Species 0.000 claims description 4
- 210000000056 organ Anatomy 0.000 claims description 4
- 241000233626 Plasmopara Species 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 241000233684 Bremia Species 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 1
- 241000302462 Albugo occidentalis Species 0.000 claims 1
- 241000233614 Phytophthora Species 0.000 claims 1
- 241001281802 Pseudoperonospora Species 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- 150000004696 coordination complex Chemical class 0.000 claims 1
- 239000000645 desinfectant Substances 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- -1 4-phenoxyphenyl Chemical group 0.000 abstract description 2
- 201000010099 disease Diseases 0.000 abstract description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 2
- 241000196324 Embryophyta Species 0.000 description 18
- 239000004480 active ingredient Substances 0.000 description 13
- 238000009472 formulation Methods 0.000 description 7
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- 239000002202 Polyethylene glycol Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 229920001223 polyethylene glycol Polymers 0.000 description 6
- 239000002689 soil Substances 0.000 description 5
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 4
- 239000005995 Aluminium silicate Substances 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 235000012211 aluminium silicate Nutrition 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 4
- 244000005700 microbiome Species 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 3
- 240000003768 Solanum lycopersicum Species 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 229920005552 sodium lignosulfonate Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241001281803 Plasmopara viticola Species 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000007931 coated granule Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 235000008504 concentrate Nutrition 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 235000020354 squash Nutrition 0.000 description 2
- 239000004546 suspension concentrate Substances 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- TWWNLDITIRCJDN-UHFFFAOYSA-N 1,2-bis(2-methylpropyl)naphthalene;sodium Chemical compound [Na].C1=CC=CC2=C(CC(C)C)C(CC(C)C)=CC=C21 TWWNLDITIRCJDN-UHFFFAOYSA-N 0.000 description 1
- MFFQGZALWIJLEJ-UHFFFAOYSA-N 2-(n-(2-methoxyacetyl)-2,6-dimethylanilino)-2-methylpropanoic acid Chemical compound COCC(=O)N(C(C)(C)C(O)=O)C1=C(C)C=CC=C1C MFFQGZALWIJLEJ-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- 240000004160 Capsicum annuum Species 0.000 description 1
- 235000008534 Capsicum annuum var annuum Nutrition 0.000 description 1
- 241000499489 Castor canadensis Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 235000008694 Humulus lupulus Nutrition 0.000 description 1
- 244000025221 Humulus lupulus Species 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 235000003228 Lactuca sativa Nutrition 0.000 description 1
- 235000011779 Menyanthes trifoliata Nutrition 0.000 description 1
- 240000008790 Musa x paradisiaca Species 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000233654 Oomycetes Species 0.000 description 1
- 241000233679 Peronosporaceae Species 0.000 description 1
- 241000233622 Phytophthora infestans Species 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 235000021015 bananas Nutrition 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
- 239000001511 capsicum annuum Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 235000021186 dishes Nutrition 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 150000002696 manganese Chemical class 0.000 description 1
- 229910052751 metal Chemical class 0.000 description 1
- 239000002184 metal Chemical class 0.000 description 1
- ZQEIXNIJLIKNTD-GFCCVEGCSA-N metalaxyl-M Chemical group COCC(=O)N([C@H](C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-GFCCVEGCSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/46—N-acyl derivatives
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/12—Powders or granules
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
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- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Carbon And Carbon Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Catalysts (AREA)
Abstract
4-[3-(4-클로로페닐)-3-(3,4-디메톡시페닐)아크릴로일]모르폴린("디메토모르프") 또는 3-아닐리노-5-메틸-5-(4-페녹시페닐)-1,3-옥사졸리딘-2,4-디온("파목사돈")과 혼합된, 70중량% 이상의 R-에난티오머의 높은 함량을 갖는 메탈락실, 또는 순수한 R-메탈락실은 메탈락실이 라세메이트의 형태로 사용되는 동일한 종류의 혼합물과 비교하여 식물 병에 대해 명백하게 증강된 살진균 작용을 나타낸다.4- [3- (4-chlorophenyl) -3- (3,4-dimethoxyphenyl) acryloyl] morpholine ("dimethomorph") or 3-anilino-5-methyl-5- ( Metallaxyl, or pure, with a high content of at least 70% by weight of R-enantiomers, mixed with 4-phenoxyphenyl) -1,3-oxazolidine-2,4-dione ("famoxadon") R-metallaxyl exhibits clearly enhanced fungicidal action against plant diseases compared to mixtures of the same kind where metallaxyl is used in the form of racemates.
Description
본 발명은 R-에난티오머 함량이 70중량% 이상인 메탈락실을 기재로 하는, 예상외로 증강된 활성을 갖는 살진균제 2성분 혼합물, 및 난균류(Oomycetes)에 의한 침범의 방제 및 예방에서의 상기 혼합물의 용도에 관한 것이다. 메탈락실 성분은 활성 성분 I로 나타낸다.The present invention provides an unexpectedly enhanced fungicide bicomponent mixture based on metallaxyl having an R-enantiomer content of at least 70% by weight, and the above mixture in the control and prevention of invasion by Oomycetes. It relates to the use of. The metallaxyl component is represented by active component I.
혼합 파트너 II는 다음 살균제 중 하나이다: IIA) 4-[3-(4-클로로페닐)-3-(3,4-디메톡시페닐)아크릴로일]모르폴린("디메토모르프")(The Pesticide Manual, 10thEd., 페이지 351-2, 1994), 또는 IIB) 3-아닐리노-5-메틸-5-(4-페녹시페닐)-1,3-옥사졸리딘-2,4-디온("파목사돈")(Brighton Crop Protection Conference, Pests & Diseases 1996, Vol. I, 페이지 21-26). 화합물 IIA 또는 IIB의 염 또는 금속 착체, 예를 들어, 구리 또는 망간 염을 사용할 수도 있다.Mixing partner II is one of the following fungicides: IIA) 4- [3- (4-chlorophenyl) -3- (3,4-dimethoxyphenyl) acryloyl] morpholine ("dimethomorph") (The Pesticide Manual, 10 th Ed., Pages 351-2, 1994), or IIB) 3-anilino-5-methyl-5- (4-phenoxyphenyl) -1,3-oxazolidine-2,4- Dion (“Sofa Pigs”) (Brighton Crop Protection Conference, Pests & Diseases 1996, Vol. I, pages 21-26). Salts or metal complexes of compounds IIA or IIB can also be used, for example copper or manganese salts.
보다 협의로, 본 발명은 R-에난티오머 함량이 85중량% 이상, 특히 92중량% 이상, 보다 특히 95중량% 이상인 순수한 메탈락실의 혼합물에 관한 것이다. 최상의 결과는 S-에난티오머를 실질적으로 함유하지 않는 순수한 R-에난티오머를 사용하여 수득된다.More specifically, the present invention relates to a mixture of pure metallaxyls having an R-enantiomer content of at least 85% by weight, in particular at least 92% by weight and more particularly at least 95% by weight. Best results are obtained using pure R-enantiomers that are substantially free of S-enantiomers.
메탈락실은 메틸 N-(2,6-디메틸페닐)-N-(메톡시아세틸)-DL-알라니네이트이고 다음 구조를 갖는다.Metallaxyl is methyl N- (2,6-dimethylphenyl) -N- (methoxyacetyl) -DL-alanine and has the structure Has
이는 비대칭성 C*원자를 가지며 통상적인 방법(GB-1 500 581)으로 에난티오머로 분리할 수 있다. 1975년 이후에 R-에난티오머의 살진균 작용이 S-에난티오머의 작용을 월등히 능가하는 것으로 당해 분야의 숙련가에게 공지되어 있으며, R-에난티오머가 실제로 진정한 활성 구조를 형성시키는 것으로 간주된다. 시판되고 있는 메탈락실은 라세메이트의 형태로 구입할 수 있다. 실용상의 이유로 절반이 목적하는 R-에난티오머로 이루어진 라세메이트를 분리할 필요가 과거에는 전혀 없었다..It has an asymmetric C * atom and can be separated into enantiomers by conventional methods (GB-1 500 581). It is known to those skilled in the art that the fungicidal action of R-enantiomers since 1975 far surpasses that of S-enantiomers, and R-enantiomers are considered to actually form the true active structure. . Commercially available metallaxyl can be purchased in the form of racemates. For practical reasons there has never been a need to separate racemates consisting of half of the desired R-enantiomers.
전혀 놀랍게도, 본 발명에 이르러, 순수한 형태 또는 라세메이트내에 70% 이상 집중된 형태의 R-메탈락실은 살균제 파트너 IIA 또는 IIB 중 하나와 협력하여, 이들 중 일부는 계수 10에 이르는 정도로 라세메이트-기재 혼합물(예를 들어, EP-280 348 또는 EP-393 911에 언급됨)의 효과를 능가하는 예상외로 고도로 증강된 효과를 달성하는 것으로 밝혀졌다. 라세메이트의 R-에난티오머 함량이 약 50%인 것을 근거로 하여 예상할 수 있는 계수는 기껏해야 2이다.Not surprisingly, according to the present invention, R-metallaxyl, either in pure form or in a form concentrated at least 70% in racemate, cooperates with one of the fungicide partners IIA or IIB, some of which are racemate-based mixtures up to a factor of 10. It has been found to achieve unexpectedly highly enhanced effects that outweigh the effects of EP-280 348 or EP-393 911. Based on the R-enantiomer content of the racemate of about 50%, the predictable coefficient is at most 2.
이러한 전혀 예상외의 결과와 함께, 본 발명은 당해 분야의 매우 실질적인 개선 및 식물 상에서의 난균류의 방제에 사용되는 살균제의 총 적용량을 감소시킴으로써 환경 보호의 가능성을 기술한다. R-에난티오머 함량이 70중량%를 초과하자마자 토양내에서의 현저하게 개선된 메탈락실의 분해성은 WO-96/01559로부터 공지되어 있다.With this unexpected result, the present invention describes the possibility of environmental protection by making very substantial improvements in the art and reducing the total application of fungicides used for controlling fungi on plants. As soon as the R-enantiomer content exceeds 70% by weight, the degradability of the significantly improved metallacyl in the soil is known from WO-96 / 01559.
2성분 혼합물 I:II에 추가하여, 본 발명은 또한 부위, 예를 들어, 진균에 의해 침범되거나 진균에 의한 침범의 위험이 있는 식물을 a) 성분 I 및 b) 화합물 II로 임의의 순서로 또는 동시에 처리함을 포함하여, 진균을 방제하는 방법에 관한 것이다.In addition to the two-component mixtures I: II, the present invention also relates to a plant, such as a) component I and b) compound II, in any order, or at the site, for example, at risk of infestation by fungi or It relates to a method for controlling fungi, including treatment at the same time.
2가지 성분의 바람직한 I:II 혼합비는 30:1 내지 1:30, 특히 10:1 내지 1:10, 보다 특히 10:1 내지 1:5이다. 다수의 경우에, 화합물 I 대 화합물 II의 혼합비가 1:1 내지 1:5인 혼합물이 유리하다.Preferred I: II mixing ratios of the two components are from 30: 1 to 1:30, in particular from 10: 1 to 1:10, more particularly from 10: 1 to 1: 5. In many cases, mixtures in which the mixing ratio of compound I to compound II is 1: 1 to 1: 5 are advantageous.
본 발명에 따른 화합물 혼합물 I+II는 경작 식물의 보호에 대해 매우 유리한 치료성, 예방성 및 침투성 살균제 특성을 갖는다. 본 발명의 화합물 혼합물을 사용하여, 식물 또는 유용 식물의 각종 작물 중 식물의 기관(열매, 꽃, 잎, 줄기, 또는 뿌리)에 발생하는 미생물을 억제하거나 구제할 수 있으며, 이후 자라나는 식물의 기관을 또한 상기 미생물로부터 보호한다. 이는 또한 특히 메탈락실에 대해 감소된 감수성을 나타내는 미생물에 적합하다.The compound mixture I + II according to the invention has very favorable therapeutic, prophylactic and penetrating fungicide properties for the protection of cultivated plants. The compound mixture of the present invention can be used to inhibit or control microorganisms occurring in the organs of plants (fruit, flowers, leaves, stems, or roots) of various crops of plants or useful plants, and then to control the organs of plants that grow. It also protects against the microorganisms. It is also particularly suitable for microorganisms which exhibit reduced sensitivity to metallaxyl.
화합물 I 및 II의 혼합물은 통상적으로 조성물 형태로 사용된다. R-메탈락실(I) 및 화합물 II는 처리할 영역 또는 식물에 동시에 또는 바로 잇따라, 필요한 경우, 제형화 기술에서 통상적인 추가의 담체, 계면활성제 또는 이외의 적용-촉진 첨가제와 함께 적용할 수 있다.Mixtures of compounds I and II are commonly used in the form of compositions. R-Metalaxyl (I) and Compound II may be applied simultaneously or immediately following the area or plant to be treated, if necessary, with additional carriers, surfactants or other application-promoting additives customary in formulation technology. .
적합한 담체 및 첨가제는 고체 또는 액체일 수 있으며 제형화 기술에서 편리한 물질, 예를 들어, 천연 또는 재생 광물질, 용제, 분산제, 습윤제, 점착부여제, 증점제, 결합제 또는 비료이다.Suitable carriers and additives may be solid or liquid and are convenient materials in the formulation art, for example natural or renewable minerals, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers.
화합물 I 및 II의 각각을 하나 이상 포함하는 화합물 혼합물을 적용하는 바람직한 방법은 토양 위의 식물의 기관, 특히 잎에의 적용이다(잎 적용). 적용 주기 및 적용량은 문제의 병원체에 대한 생물학적 및 기후상 생존 조건에 따라 달라진다. 화합물은 또한 식물의 부위를 액체 제제에 함침시킨 결과로서 또는 화합물을 고체 형태, 예를 들어, 과립 형태로 토양에 주입함으로써 토양을 경유하여(침투 작용) 뿌리 기관을 통하여 식물로 침투시킬 수 있다(토양 적용).A preferred method of applying a compound mixture comprising at least one of each of compounds I and II is the application of plants on the soil, in particular to leaves (leaving applications). The frequency of application and the amount of application depend on the biological and climatic survival conditions for the pathogen in question. The compound may also penetrate into the plant via the root organs via the soil (infiltration) either as a result of impregnating the site of the plant with the liquid formulation or by injecting the compound into the soil in solid form, for example in the form of granules ( Soil application).
배합물 중의 화합물은 변형되지 않은 형태로 또는 바람직하게는 제형화 기술에서 통상적으로 사용되는 보조제와 함께 사용하여, 공지된 방식으로 유화성 농축액, 피복성 페이스트, 직접 분무가능하거나 희석가능한 용제, 희석 유화제, 습윤성 산제, 가용성 산제, 분제 또는 과립제로 제형화시키거나 물질, 예를 들어, 중합체 물질내에 캡슐화시킴으로써 제형화시킨다. 조성물의 특성에 따라, 분무, 분취, 산포, 산란, 도포 또는 주입과 같은 적용 방법은 의도한 목표 및 우세한 환경에 적합하도록 선택한다. 화합물 혼합물의 바람직한 적용량은 일반적으로 헥타(ha)당 활성 성분(a.i.) 50g 내지 1800g, 특히 100g 내지 1000g a.i./ha이다.The compounds in the formulation can be used in unmodified form or preferably in combination with auxiliaries commonly used in formulation techniques, in known manner emulsifiable concentrates, coating pastes, directly sprayable or dilutable solvents, dilute emulsifiers, Formulated by wettable powders, soluble powders, powders or granules or by encapsulation in a material, for example a polymeric material. Depending on the nature of the composition, the method of application, such as spraying, preparative, scattering, scattering, applying or injecting, is selected to suit the intended goal and prevailing environment. The preferred application amount of the compound mixture is generally from 50 g to 1800 g, in particular from 100 g to 1000 g a.i./ha of the active ingredient (a.i.) per hectare (ha).
제형은 공지된 방식으로, 예를 들어, 활성 성분을 용제, 고체 담체 및, 필요한 경우, 표면-활성 화합물(계면활성제)과 같은 증량제와 균질 혼합 및/또는 분쇄시킴으로써 제조한다.The formulations are prepared in a known manner, for example by homogeneously mixing and / or grinding the active ingredient with a solvent, a solid carrier and, if necessary, an extender such as a surface-active compound (surfactant).
농화학적 조성물은 통상적으로 화학식 I 및 II의 화합물을 0.1 내지 99중량%, 특히 0.1 내지 95중량%, 고체 또는 액체 보조제를 99.9 내지 1중량%, 특히 99.9 내지 5중량%, 및 계면활성제를 0 내지 25중량%, 특히 0.1 내지 25중량% 함유한다.Agrochemical compositions typically comprise from 0.1 to 99%, in particular from 0.1 to 95% by weight of the compounds of formulas (I) and (II), from 99.9 to 1% by weight of solid or liquid auxiliaries, in particular from 99.9 to 5% by weight, and from 0 to 0% of surfactant. 25% by weight, in particular 0.1 to 25% by weight.
시판품은 바람직하게는 농축물로서 제형화되므로, 최종 사용자는 통상적으로 희석 제형을 사용한다.Commercially available products are preferably formulated as concentrates, so end users typically use dilute formulations.
적합한 표적 작물은 특히 감자, 포도나무, 홉, 옥수수, 사탕무, 담배, 채소(토마토, 파프리카, 상추 등), 및 또한 바나나, 고무, 잔디풀 및 장식용 식물이다. 솜털 곰팡이에 의해 멸종 위기에 있는 이외의 식물은 특히 메탈락실에 관한 문헌으로부터 공지되어 있다.Suitable target crops are especially potatoes, vines, hops, corn, sugar beets, tobacco, vegetables (tomatoes, paprika, lettuce, etc.), and also bananas, gums, grasses and ornamental plants. Plants other than those endangered by downy mildew are known in particular from the literature on metallaxyl.
다음 실시예는 본 발명을 예시하는 것이며, "활성 성분"은 특정 혼합비의 메탈락실(R-메탈락실 함량이 95중량% 이상임) 및 화합물 II의 혼합물을 의미한다.The following examples illustrate the invention, where "active ingredient" means a mixture of metallaxyl (with R-metallaxyl content of at least 95% by weight) and compound II in a specific mixing ratio.
습윤성 산제 a) b) c)Wettable powder a) b) c)
활성 성분[I:IIA = 1:1(a),Active ingredient [I: IIA = 1: 1 (a),
1:10(b); I:IIB = 1:5(c)] 26% 44% 72%1:10 (b); I: IIB = 1: 5 (c)] 26% 44% 72%
나트륨 리그노설포네이트 5% 5% -Sodium Lignosulfonate 5% 5%-
나트륨 라우릴 설페이트 3% - 5%Sodium Lauryl Sulfate 3%-5%
나트륨 디이소부틸나프탈렌 설포네이트 - 6% 10%Sodium Diisobutylnaphthalene Sulfonate-6% 10%
옥틸페놀 폴리에틸렌 글리콜 에테르 - 2% -Octylphenol Polyethylene Glycol Ether-2%-
(에틸렌 옥사이드 7-8mol)(Ethylene oxide 7-8mol)
고도로 분산된 규산 6% 13% 13%Highly dispersed silicic acid 6% 13% 13%
카올린 60% 30% -Kaolin 60% 30%-
활성 성분을 보조제와 함께 완전히 혼합하고 혼합물을 적합한 밀로 완전히 분쇄시켜, 물로 희석가능한 습윤성 산제를 수득하여 목적하는 농도의 현탁제를 제공한다.The active ingredient is thoroughly mixed with the adjuvant and the mixture is thoroughly milled into a suitable mill to give a wettable powder dilutable with water to provide a suspending agent of the desired concentration.
유화성 농축액Emulsifiable concentrate
활성 성분(I:IIA 또는 IIB = 2:1) 12%12% active ingredient (I: IIA or IIB = 2: 1)
옥틸페놀 폴리에틸렌 글리콜 에테르(에틸렌 옥사이드 4-5mol) 3%Octylphenol polyethylene glycol ether (ethylene oxide 4-5mol) 3%
칼슘 도데실벤젠설포네이트 3%Calcium Dodecylbenzenesulfonate 3%
비버유 폴리글리콜 에테르(에틸렌 옥사이드 35mol) 4%Beaver oil polyglycol ether (35 mol ethylene oxide) 4%
사이클로헥사논 30%Cyclohexanone 30%
크실렌 혼합물 48%Xylene Mixture 48%
식물 보호에 사용가능한 목적하는 희석도의 유화제를 물로 희석시킴으로써 상기 농축액으로부터 수득할 수 있다.The emulsifiers of the desired dilution usable for plant protection can be obtained from the concentrate by dilution with water.
압출 과립제Extruded granules
활성 성분(I:IIA = 1:1) 16%Active ingredient (I: IIA = 1: 1) 16%
나트륨 리그노설포네이트 2%Sodium lignosulfonate 2%
카복시메틸셀룰로스 1%Carboxymethylcellulose 1%
카올린 81%Kaolin 81%
활성 성분을 혼합하고 보조제와 함께 혼합한 다음, 혼합물을 물로 습윤화시킨다. 당해 혼합물을 압출시킨 다음 공기 스트림내에서 건조시킨다.The active ingredient is mixed and mixed with the adjuvant, and then the mixture is wetted with water. The mixture is extruded and then dried in an air stream.
피복된 과립제Coated granules
활성 성분(I:IIB = 10:1) 11%Active ingredient (I: IIB = 10: 1) 11%
폴리에틸렌 글리콜(200mol.중량) 3%Polyethylene glycol (200 mol. Weight) 3%
카올린 86%Kaolin 86%
미세하게 분쇄된 활성 성분을 균일하게 혼합기내에서 폴리에틸렌 글리콜로 습윤화시킨 카올린에 도포한다. 비-산포성 피복된 과립제를 상기 방법으로 수득한다.The finely ground active ingredient is applied to kaolin, which is wetted with polyethylene glycol in a uniform mixer. Non-dispersible coated granules are obtained by the above method.
현탁제 농축액Suspension Concentrate
활성 성분(I:IIA 또는 IIB = 1:10) 44%Active ingredient (I: IIA or IIB = 1:10) 44%
폴리에틸렌 글리콜 10%Polyethylene Glycol 10%
노닐페놀 폴리에틸렌 글리콜 에테르(에틸렌 옥사이드 15mol) 6%Nonylphenol Polyethylene Glycol Ether (15 mol ethylene oxide) 6%
나트륨 리그노설포네이트 10%Sodium Lignosulfonate 10%
카복시메틸셀룰로스 1%Carboxymethylcellulose 1%
실리콘유(75% 수성 유화액 형태) 1%1% silicone oil (75% aqueous emulsion form)
물 28%Water 28%
미세하세 분쇄된 활성 성분을 보조제와 균질 혼합하여, 물로 희석함으로써 수득가능한 목적하는 희석도의 현탁액으로부터 현탁제 농축액을 제공한다. 상기 희석액을 사용하여, 생존하는 식물을 분무, 관수 또는 침지에 의해 미생물에 의한 침범으로부터 처치하고 보호할 수 있다.The finely divided milled active ingredient is homogeneously mixed with the adjuvant to provide a suspension concentrate from a suspension of the desired dilution obtainable by dilution with water. The diluent can be used to treat and protect surviving plants from invasion by microorganisms by spraying, irrigation or dipping.
생물학적 실시예Biological Example
실시예 1) 포도나무 상의 플라스모파라 비티콜라(Plasmopara viticola)에 대한 작용Example 1 Actions on Plasmopara viticola on Vine
구테델 품종의 포도나무 묘목을 온실 조건(20-24℃)하에 4- 내지 5-엽기(3주)로 생장시킨다. 다음, 직경 10mm의 디스크를 잎으로부터 잘라낸다. 잎 조각을 이의 윗면이 아래로 향하게 하여 페트리 디쉬에 둔다. 당해 디쉬는 1.8ml 물/0.16% 아가를 함유한다. 살진균제를 탈염수에 가하여 적합하게 희석시킨다. 살진균체 처치를 접종 하루 전에 수행한다. 다음, 전체 잎 표면 디스크에 갓 제조한 플라스모파라 비티콜라의 포자낭 현탁액(50000-60000/ml)을 방울 방울 흘러내리도록 분무한다. 후속적으로 상기 식물을 18℃ 및 약 100% 상대 습도에서 12시간의 인공 일광(3000럭스)을 비추면서 7일 동안 조절된 환경 챔버내에 방치한다. 다음, 침범도의 평가를 수행한다.Vine seedlings of the Gutedel variety are grown in 4- to 5-leaf stages (3 weeks) under greenhouse conditions (20-24 ° C.). Next, a disk with a diameter of 10 mm is cut out of the leaves. Place leaf pieces in Petri dishes with their top side down. The dish contains 1.8 ml water / 0.16% agar. Fungicides are added to demineralized water and diluted appropriately. Fungicide treatment is performed one day prior to inoculation. Next, a spore sac suspension of freshly prepared Plasmopara viticola (50000-60000 / ml) is sprayed onto the entire leaf surface disc to drop down. The plant is subsequently left in a controlled environmental chamber for 7 days with 12 hours of artificial sunlight (3000 lux) at 18 ° C. and about 100% relative humidity. Next, an evaluation of the degree of infringement is performed.
잎 침범율을 평가하고 대조군에 비례한 작용율을 계산한다. 혼합물 R-메탈락실(〉95중량%)/파목사돈 및 혼합물 메탈락실(라세메이트)/파목사돈과의 비교로 비교 계수를 제공한다.The leaf invasion rate is assessed and the action rate proportional to the control is calculated. Comparison coefficients are provided by comparison with the mixture R-metallaxyl (> 95% by weight) / paroxone and the mixture metallaxyl (racemate) / paroxone.
실시예 2) 토마토 상의 파이토프토라 인페스탄스(Phytophthora infestans)에 대한 작용Example 2 Action on Phytophthora infestans on Tomato
품종 cv. 베이비(Baby)의 토마토 묘목을 각각 화분(직경 = 8cm)에서 온실 조건하에 4주 동안 생장시킨다. 다음, 식물에 유화성 농축액으로부터 제조된 활성 성분 제형을 분무시킨다. 3그루 묘목을 각각의 경우에 사용한다. 식물의 아래쪽 잎의 전체 잎 표면에 갓 제조한 플라스모파라 인페스탄스의 포자낭 현탁액(80000/ml)을 분무한다. 후속적으로 상기 식물을 18℃ 및 약 100% 상대 습도에서 16시간의 인공 일광을 비추면서 2일 동안 및 15℃ 및 60% 상대 습도에서 추가 5일 동안 방치한다. 다음, 침범도의 평가를 수행한다.Varieties cv. Baby tomato seedlings are grown in pots (diameter = 8 cm) for 4 weeks under greenhouse conditions. The plants are then sprayed with the active ingredient formulations prepared from emulsifiable concentrates. Three seedlings are used in each case. Spray a freshly prepared spore sac suspension (80000 / ml) of Plasmopara infestans on the entire leaf surface of the bottom leaf of the plant. The plant is subsequently left for 2 days with 16 hours of artificial sunlight at 18 ° C. and about 100% relative humidity and for an additional 5 days at 15 ° C. and 60% relative humidity. Next, an evaluation of the degree of infringement is performed.
잎 침범율을 평가하고 대조군에 비례한 작용율을 계산한다. 혼합물 R-메탈락실(〉95중량%)/디메토모르프 및 혼합물 메탈락실(라세메이트)/디메토모르프와의 비교로 비교 계수를 제공한다.The leaf invasion rate is assessed and the action rate proportional to the control is calculated. Comparison coefficients are provided by comparison with the mixture R-metallaxyl (> 95% by weight) / dimethomorph and the mixture metallaxyl (racemate) / dimethomorph.
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CN101642109B (en) * | 2009-09-08 | 2013-02-06 | 东莞市瑞德丰生物科技有限公司 | Bactericidal composition containing famoxadone |
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